Polymers containing strongly acidic or basic groups are useful as ion-exchange resins, and for other uses. Sulfonic acid containing polymers are useful as ion-exchange resins and as strong acid catalysts. Polymers which are fluorinated may also be more thermally and/or chemically resistant than unfluorinated polymers, so fluorinated sulfonic acid containing polymers may be particularly useful. Such polymers are useful in the form of films, coatings, membranes, other shaped articles and particles.
For use as an ion exchange resin or strong acid catalyst resin, it is generally preferred if the resin contains as many active sites as possible. It is known in the art (see, for instance, U.S. Pat. No. 4,948,844) that it is difficult to (co)polymerize perfluorinated (alkyl vinyl ethers), while fluorinated alkyl vinyl ethers which contain some hydrogen in the alkyl group, particularly alpha to the ether oxygen, are more readily polymerizable, and can be (co)polymerized to give polymers with high vinyl ether contents.
Yu. E. Kirsh, et al., Russian Chemical Rev., vol. 59, p. 560-574 (1990) have reviewed the literature of perfluorinated cation exchange membranes.
U.S. Pat. No. 4,597,913 describes the synthesis of certain perfluorinated (with the exception of the "R" group on the sulfur) sulfide containing vinyl ethers, (co)polymers containing those vinyl ethers as repeat units, and oxidation of the (co)polymers to obtain the analogous sulfonic acid containing perfluorinated polymers. No mention is made of partially fluorinated sulfonic acid containing polymers.
T. Nguyen, et al., Eur. Polym. J., vol. 27, p. 435-438 (1991) describe the preparation of certain perfluorinated (with the exception of the "R" group on sulfur) sulfide containing vinyl ethers and their conversion to sulfonyl chlorides. No mention is made of the novel compounds described herein.
U.S. Pat. No. 5,206,440 describes the oxidation of organofluorine containing sulfides to sulfones using a fluorine/acetonitrile/water reagent. S. Rozen, et al., J. Chem. Soc., Chem. Commun., p. 1959 (1994) describes the oxidation of thiophenes to S,S-dioxides using a fluorine/acetonitrile/water reagent.